4,4′-(Oxydimethyl­ene)dibenzonitrile

Jie Xiao; Hong Zhao

doi:10.1107/S1600536808020527

. 2008 Jul 9;64(Pt 8):o1436. doi: 10.1107/S1600536808020527

4,4′-(Oxydimethylene)dibenzonitrile

Jie Xiao ^a, Hong Zhao ^a,^*

PMCID: PMC2962067 PMID: 21203151

Abstract

The title compound, C₁₆H₁₂N₂O, was accidentally synthesized by the reaction of 4-(bromomethyl)benzonitrile and pentaerythritol. The dihedral angle between the benzene rings is 57.39 (9)°. In the crystal structure, molecules are linked by intermolecular C—H⋯N hydrogen-bonding interactions to form chains running parallel to the b axis.

Related literature

For applications of nitrile derivatives in the synthesis of some heterocyclic molecules, see: Radl et al. (2000 ▶); Jin et al. (1994 ▶). For the crystal structure of a related compound, see: Fu & Zhao (2007 ▶).

Experimental

Crystal data

C₁₆H₁₂N₂O
M _r = 248.28
Monoclinic,
a = 14.444 (3) Å
b = 7.6674 (13) Å
c = 11.897 (2) Å
β = 96.326 (14)°
V = 1309.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.35 × 0.30 × 0.30 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.939, T _max = 0.978
13064 measured reflections
3007 independent reflections
1498 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.149
S = 1.01
3007 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020527/rz2229sup1.cif

e-64-o1436-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020527/rz2229Isup2.hkl

e-64-o1436-Isup2.hkl^{(147.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N2ⁱ	0.93	2.60	3.490 (3)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to HZ.

supplementary crystallographic information

Comment

Nitrile derivatives are an important class of compounds used in the chemical industry. For example, nitrile derivatives are employed in the synthesis of some heterocyclic molecules (Radl et al., 2000), and have been used as starting materials for the synthesis of phthalocyanines (Jin et al., 1994). Recently, we have reported the crystal structure of a benzonitrile compound (Fu & Zhao, 2007). The title compound was unexpectedly obtained during our work on nitrile compounds, and its crystal structure is reported here.

In the title compound (Fig. 1), bond lengths and angles have normal values. The planes through the C2—C7 and C10—C15 benzene rings form a dihedral angle of 57.39 (9)°. The crystal structure is stabilized by an intermolecular C—H···N hydrogen bond forming chains of molecules along the b-axis (Table 1).

Experimental

Pentaerythritol (0.136 g, 1 mmol) and 4-(bromomethyl)benzonitrile (0.658 g, 4 mmol) were dissolved in water in the presence of sodium hydroxide (0.160 g, 4 mmol) and heated under reflux for 2 days. After the mixture was cooled to room temperature, the solvent was removed in vacuum to afford a white precipitate of the title compound. Colourless crystals suitable for X-ray diffraction were obtained from a solution of 100 mg in 15 ml diethylether by slow evaporation after 5 days.